Can you live with just MacOS in the shack or is Windows a must?
I have worked in the local phone company (now a broadband company) for almost 25 years. I sold and worked on computers for a few years prior to going to work there, so in total I have been working with/on computers for almost 30 years. Started with TRSDOS and moved to MS-DOS, then Windows 3.11. Next to expand my OS knowledge I spent some time running SCO UNIX, then back to Windows (95b I think). Off to Linux for a bit running Redhat. Then back to Windows and finally 3 years ago I tried Mac OS. I love my iPhone and thought it would be good synergy, and it is!
Just about everything I want to do related to Amateur Radio, I have been able to find a program that runs on the MAC. For radio programming I use Chirp. For logging/contesting I use MacLoggerDX.